John Legend

For an unknown artist to choose the surname "Legend" suggests a level of swagger at odds with John Legend's smooth, timeless R&B. However, his six Grammy Awards and his roll call of collaborators — the late Michael Jackson, Stephen Colbert and Apple CEO Steve Jobs, for starters — show the self-confidence John Stephens had at the start of his decadelong career was justified. The Springfield, Ohio, native has fit three acclaimed albums into his long list of Legend-ary extracurricular activities. 2008's Evolver, which experimented with synths and randier lyrics, is his most recent release; a new set, featuring live hip-hop icons the Roots, is reportedly due later this year.